CN110225917B - New compound and organic light-emitting device using it - Google Patents

Abstract

The present invention relates to novel compounds and organic light-emitting devices using them.

Description

New compound and organic light-emitting device using it

technical field

Cross References to Related Applications

This application claims the benefit of priority from Korean Patent Application No. 10-2017-0056389 filed on May 2, 2017, the entire disclosure of which is incorporated herein by reference.

The present invention relates to novel compounds and organic light-emitting devices comprising them.

Background technique

Generally, the organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy by using an organic material. An organic light emitting device utilizing the organic light emitting phenomenon has characteristics such as a wide viewing angle, excellent contrast, fast response time, and excellent luminance, driving voltage, and response speed, and thus many studies have been conducted.

An organic light emitting device generally has a structure including an anode, a cathode, and an organic material layer interposed between the anode and the cathode. The organic material layer usually has a multilayer structure containing different materials to improve the efficiency and stability of the organic light-emitting device, for example, the organic material layer can be composed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer And so formed. In the structure of an organic light emitting device, if a voltage is applied between two electrodes, holes are injected from the anode into the organic material layer, electrons are injected from the cathode into the organic material layer, and when the injected holes and electrons meet each other, Excitons are formed, and light is emitted when the excitons fall to the ground state again.

There has been a need to develop new materials for organic materials used in such organic light emitting devices.

[Prior art literature]

[Patent Document]

(Patent Document 0001) Korean Patent Laid-Open No. 10-2000-0051826

Contents of the invention

technical problem

The present invention relates to novel compounds and organic light-emitting devices comprising them.

Technical solutions

The present invention provides compounds represented by the following formula 1 or comprising structural units represented by the following formula 1:

[Formula 1]

Among them, in formula 1,

Rings _A1 to _A3 are each independently a _C6-20 aromatic ring or a _C2-60 heteroaromatic ring comprising at least one heteroatom selected from N, O and S,

R _a , R _b and R ₁ to R ₃ are each independently hydrogen; deuterium; halogen; cyano; nitro; substituted or unsubstituted silyl; substituted or unsubstituted amino; substituted or Unsubstituted C _1-60 alkyl; substituted or unsubstituted C _1-60 haloalkyl; substituted or unsubstituted C _1-60 alkoxy; substituted or unsubstituted C _{1- 60} haloalkoxy; substituted or unsubstituted C _3-60 cycloalkyl; substituted or unsubstituted C _2-60 alkenyl; substituted or unsubstituted C _6-60 aryl; substituted or an unsubstituted C _6-60 aryloxy group; or a substituted or unsubstituted C _2-60 heteroaryl group comprising at least one heteroatom selected from N, O and S,

The prerequisite is that at least one of R _a , R _b and R ₁ to R ₃ is a substituted or unsubstituted silyl group, or is substituted by a silyl group,

R _a can be connected to ring A 1 or _{A 3 through} a single bond, -O-, -S-, -C(Q ₁ )(Q ₂ )- or -N(Q ₃ )-,

R _b may be attached to ring A ₂ or A ₃ via a single bond, -O-, -S-, -C(Q ₄ )(Q ₅ )-, or -N(Q ₆ )-, and

Rings A ₁ and A ₂ can be connected to each other via a single bond, -O-, -S-, -C(Q ₇ )(Q ₈ )- or -N(Q ₉ )-,

Wherein Q ₁ to Q ₉ are each independently hydrogen; deuterium; C _1-10 alkyl; or C _6-20 aryl, and

n1 to n3 are each independently an integer of 0 to 10.

The present invention also provides an organic light-emitting device, which includes: a first electrode; a second electrode disposed on the side opposite to the first electrode; and at least one organic material layer disposed between the first electrode and the second electrode , wherein at least one of the organic material layers contains the compound represented by Formula 1.

Beneficial effect

The above compound represented by Formula 1 may be used as a material of an organic material layer of an organic light emitting device, and when applied to an organic light emitting device, improves efficiency, low driving voltage, and/or improves lifetime characteristics.

Description of drawings

FIG. 1 shows an example of an organic light emitting device including a substrate 1 , an anode 2 , a light emitting layer 3 and a cathode 4 .

FIG. 2 shows an example of an organic light emitting device including a substrate 1 , an anode 2 , a hole injection layer 5 , a hole transport layer 6 , a light emitting layer 7 , an electron transport layer 8 and a cathode 4 .

Fig. 3 is a graph measuring the absorption peak wavelength of Compound 1 by spectrofluorometry.

Fig. 4 is a graph measuring the half-value width of Compound 1 by spectrofluorometry.

Detailed ways

Hereinafter, the present invention will be described in more detail to help understanding of the present invention.

意指与另外的取代基连接的键。In this manual,

means a bond to another substituent.

The term "substituted or unsubstituted" as used herein means to be substituted with one or more substituents selected from: deuterium; halo group; cyano group; nitro group; hydroxyl group; carbonyl group; ester group; imido; amino; phosphine oxide; alkoxy; aryloxy; alkylthio; arylthio; alkylsulfonyl; arylsulfonyl; silyl; boryl; alkyl; ring Alkyl; alkenyl; aryl; aralkyl; arylalkenyl; alkylaryl; alkylamine; aralkylamine; heteroarylamine; arylamine; A heterocyclic group comprising at least one of N, O, and S atoms, or there is no substituent, or it is substituted by a substituent in which two or more substituents of the exemplified substituents are connected, or there is no Substituents are present. For example, the term "substituent in which two or more substituents are linked" may be biphenyl. That is, the biphenyl group may be an aryl group, or may be understood as a substituent in which two phenyl groups are connected.

In the present specification, the number of carbon atoms in the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the carbonyl group may be a compound having the following structure, but is not limited thereto.

In this specification, the ester group may have a structure in which the oxygen of the ester group may be replaced by a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms replace. Specifically, the ester group may be a compound having the following structure, but is not limited thereto.

In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the imide group may be a compound having the following structure, but is not limited thereto.

In this specification, the silyl group specifically includes trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc., but not limited thereto.

In this specification, the boron group specifically includes trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, phenylboryl, etc., but is not limited thereto.

In this specification, examples of the halogen group include fluorine, chlorine, bromine and iodine.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to yet another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of alkyl groups include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl -2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-Dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 40. According to one embodiment, alkenyl has 2 to 20 carbon atoms. According to another embodiment, alkenyl has 2 to 10 carbon atoms. According to yet another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl Base, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylethenyl-1-yl, 2-phenylethenyl-1-yl, 2, 2-Diphenylethenyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)ethenyl-1-yl, 2,2-bis(diphenyl-1-yl)ethenyl -1-yl, stilbene, styryl, etc., but not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but the number of carbon atoms thereof is preferably 3 to 60. According to one embodiment, cycloalkyl has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, cycloalkyl has 3 to 6 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclopentyl, Hexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but not limited thereto.

基、芴基等，但不限于此。In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to another embodiment, the aryl group has 6 to 20 carbon atoms. As a monocyclic aryl group, the aryl group may be phenyl, biphenyl, terphenyl, etc., but is not limited thereto. Examples of polycyclic aryl groups include naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl,

group, fluorenyl group, etc., but not limited thereto.

等。然而，结构不限于此。In this specification, a fluorenyl group may be substituted, and two substituents may be connected to each other to form a spiro ring structure. In the case of substituted fluorenyl groups, it is possible to form

Wait. However, the structure is not limited thereto.

唑基、

二唑基、三唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并

唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、苯并呋喃基、菲咯啉基、噻唑基、异

唑基、

二唑基、噻二唑基、苯并噻唑基、吩噻嗪基、二苯并呋喃基等，但不限于此。In the present specification, a heteroaryl group is a heteroaryl group containing at least one of O, N, Si and S as a heteroatom, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 60. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl,

Azolyl,

Diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazine Base, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo

Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuryl, phenanthrolinyl, thiazolyl, iso

Azolyl,

Oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzofuryl, etc., but not limited thereto.

In the present specification, the aryl group in the aralkyl group, arylalkenyl group, alkylaryl group, and arylamino group is the same as the above-mentioned examples of the aryl group. In the present specification, the alkyl group in the aralkyl group, alkylaryl group and alkylamine group is the same as the above-mentioned examples of the alkyl group. In this specification, the heteroaryl group in the heteroarylamine can be applied to the above description of the heteroaryl group. In the present specification, the alkenyl group in the aralkenyl group is the same as the above-mentioned examples of the alkenyl group. In this specification, the above description of the aryl group can be applied except that the arylene group is a divalent group. In this specification, the above description of the heteroaryl group can be applied except that the heteroarylene group is a divalent group. In the present specification, the above description of the aryl group or the cycloalkyl group can be applied except that the hydrocarbon ring is not a monovalent group but is formed by combining two substituents. In the present specification, the above description of the heteroaryl group can be applied except that the heterocyclic ring is not a monovalent group but is formed by combining two substituents.

Meanwhile, the present invention provides a compound represented by Formula 1 or a compound comprising a structural unit represented by Formula 1.

As used herein, a compound comprising a structural unit represented by Formula 1 refers to a compound comprising at least one monovalent group derived from a structural unit represented by Formula 1, or by sharing rings A ₁ to A ₃ of Formula 1 Compounds fused with at least one ring.

In addition, the compound represented by Formula 1 or the compound including the structural unit represented by Formula 1 has at least one substituted or unsubstituted silyl group, or a group substituted with at least one silyl group.

Here, the silyl group means all of the following substituents: tri(C _1-60 alkyl) silyl; substituted or unsubstituted tri(C _6-60 aryl) silyl; substituted or unsubstituted Substituted bis(C _1-60 alkyl)(C _6-60 aryl)silyl; and substituted or unsubstituted (C _1-60 alkyl)bis(C _6-60 aryl)methyl Silyl.

In addition, amino includes all of the following substituents: mono-(C _1-60 alkyl) amino or di-(C _1-60 alkyl) amino; mono-(C _6-60 aryl) amino or di-(C _{6 -60} aryl) amino; mono-(C _2-60 heteroaryl) amino or di-(C _2-60 heteroaryl) amino; (C _1-60 alkyl) (C _6-60 aryl) amino and (C _6-60 aryl) (C _2-20 heteroaryl) amino.

In Formula 1, the rings A ₁ to A ₃ may each independently be a benzene ring, a naphthalene ring, a carbazole ring, a dibenzofuran ring, or a dibenzothiophene ring.

Specifically, the compound represented by Formula 1 may be represented by one of the following Formulas 1-1 to 1-13:

Among them, in formulas 1-1 to 1-13,

X ₁ and X ₂ are each independently O, S or N(C _6-20 aryl),

L ₁ to L ₅ are each independently a single bond, -O-, -S-, -C(C _1-4 alkyl)(C _1-4 alkyl)-, or -N(C _6-20 aryl )-,

R _a1 to R _a6 , R _b1 to R _b6 , R ₁₁ to R ₁₆ , R ₂₁ to R ₂₆ and R ₃₁ to R ₃₅ are each independently hydrogen; deuterium; halogen; substituted or unsubstituted tri(C _{1 -20} alkyl) silyl; substituted or unsubstituted tri(C _6-20 aryl) silyl; substituted or unsubstituted di(C _6-20 aryl) amino; substituted or Unsubstituted (C _6-20 aryl) (C _2-20 heteroaryl) amino; substituted or unsubstituted C _1-20 alkyl; substituted or unsubstituted C _1-20 haloalkyl ; substituted or unsubstituted C _1-20 alkoxy; substituted or unsubstituted C _1-20 haloalkoxy; substituted or unsubstituted C _6-20 aryl; substituted or unsubstituted A substituted C _6-20 aryloxy group; or a substituted or unsubstituted C _2-20 heteroaryl group containing at least one heteroatom selected from N, O and S, wherein R _a1 to R _a6 and R _b1 Adjacent substituents to R _b6 may be connected to each other to form a substituted or unsubstituted _C6-20 aromatic ring,

The proviso is that in one formula at least one of R _a1 to R _a6 , R _b1 to R _b6 , R ₁₁ to R ₁₆ , R ₂₁ to R ₂₆ and R ₃₁ to R ₃₅ is a substituted or unsubstituted tri (C _1-20 alkyl) silyl group, or substituted or unsubstituted tri(C _6-20 aryl) silyl group, or tri(C _1-20 alkyl) silyl group or tri( C _6-20 aryl) silyl substitution.

For example, in Formulas 1-1 to 1-13, X ₁ and X ₂ may each independently be O, S, or N(C ₆ H ₅ ).

Furthermore, in Formulas 1-1 to 1-13, L ₁ to L ₄ may each independently be a single bond, -O-, -S-, or -C(CH ₃ ) ₂ -, and L ₅ may be - N(C ₆ H ₅ )-.

Furthermore, in formulas 1-1 to 1-13, at least one of R _a1 to R _a6 , R _b1 to R _b6 , R ₁₁ to R ₁₆ , R ₂₁ to R ₂₆ , and R ₃₁ to R ₃₅ in one formula Or may be -Si(CH ₃ ) ₃ or -Si(C ₆ H ₅ ) ₃ , or may be substituted by -Si(CH ₃ ) ₃ or -Si(C ₆ H ₅ ) ₃ .

In addition, in Formulas 1-1 to 1-13, R _a1 to R _a6 , R _b1 to R _b6 , R ₁₁ to R ₁₆ , R ₂₁ to R ₂₆ and R ₃₁ to R ₃₅ may each independently be hydrogen, deuterium , halogen, -Si(CH ₃ ) ₃ , -Si(C ₆ H ₅ ) ₃ , -CH ₃ , -CH(CH ₃ ) ₂ , -C(CH ₃ ) ₃ , -CF ₃ , or -OCF ₃ , and can be selected from:

wherein Ph means phenyl.

Specifically, for example, the compound represented by Formula 1 may be represented by any one of the following Formulas 1-1A to 1-13A:

Among them, in formulas 1-1A to 1-13A,

X ₁ , X ₂ , L ₁ to L ₅ , R _a1 to R _a4 , R _b1 to R _b4 , R ₁₂ , R ₁₃ , R ₂₂ , R ₂₃ and R ₃₂ are as shown in formulas 1-1 to 1-13, respectively limited,

The prerequisite is that in one formula at least one of R _a1 to R _a4 , R _b1 to R _b4 , R ₁₂ , R ₁₃ , R ₂₂ , R ₂₃ and R ₃₂ is -Si(CH ₃ ) ₃ or -Si( C ₆ H ₅ ) ₃ , or substituted by -Si(CH ₃ ) ₃ or -Si(C ₆ H ₅ ) ₃ .

Meanwhile, the compound including the structural unit represented by Formula 1 may be represented by one of the following Formulas 2-1 to 2-7:

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

[Formula 2-7]

Among them, in formulas 2-1 to 2-7,

R _a1 to R _a10 , R _b1 to R _b10 , R ₁₁ to R ₁₈ , R ₂₁ to R ₂₈ and R ₃₁ to R ₃₆ are each independently hydrogen; deuterium; halogen; substituted or unsubstituted tri(C _{1 -20} alkyl) silyl; substituted or unsubstituted tri(C _6-20 aryl) silyl; substituted or unsubstituted C _1-20 alkyl; substituted or unsubstituted C _1-20 haloalkyl; substituted or unsubstituted C _1-20 alkoxy; substituted or unsubstituted C _1-20 haloalkoxy; substituted or unsubstituted C _6-20 aryl ; a substituted or unsubstituted C _6-20 aryloxy group; or a substituted or unsubstituted C _2-20 heteroaryl group comprising at least one heteroatom selected from N, O and S, wherein R _a1 Adjacent substituents in to R _a6 and R _b1 to R _b6 may be connected to each other to form a substituted or unsubstituted C _6-20 aromatic ring,

The proviso is that in one formula at least one of R _a1 to R _a10 , R _b1 to R _b10 , R ₁₁ to R ₁₈ , R ₂₁ to R ₂₈ and R ₃₁ to R ₃₆ is a substituted or unsubstituted tri (C _1-20 alkyl) silyl or substituted or unsubstituted tri (C _6-20 aryl) silyl, or tri (C _1-20 alkyl) silyl or tri (C _6-20 aryl) silyl substitution.

For example, in Formulas 2-1 to 2-7, at least one of R _a1 to R _a10 , R _b1 to R _b10 , R ₁₁ to R ₁₈ , R ₂₁ to R ₂₈ and R ₃₁ to R ₃₆ is —Si (CH ₃ ) ₃ , or may be substituted by —Si(CH ₃ ) ₃ .

Furthermore, in Formulas 2-1 to 2-7, R _a1 to R _a10 , R _b1 to R _b10 , R ₁₁ to R ₁₈ , R ₂₁ to R ₂₈ , and R ₃₁ to R ₃₆ may each independently be hydrogen, - Si(CH ₃ ) ₃ or —CH ₃ .

Specifically, for example, a compound including a structural unit represented by Formula 1 may be represented by one of the following Formulas 2-1A to 2-7A:

[Formula 2-1A]

[Formula 2-2A]

[Formula 2-3A]

[Formula 2-4A]

[Formula 2-5A]

[Formula 2-6A]

[Formula 2-7A]

Among them, in formulas 2-1A to 2-7A,

R _a1 to R _a3 , R _a8 , R _b1 to R _b3 , R _b8 , R ₁₂ , R ₁₆ , R ₂₂ , R ₂₆ , R ₃₂ and R ₃₅ are as defined in formulas 2-1 to 2-7, respectively,

The prerequisite is that in one formula at least one of R _a1 to R _a3 , R _a8 , R _b1 to R _b3 , R _b8 , R ₁₂ , R ₁₆ , R ₂₂ , R ₂₆ , R ₃₂ and R ₃₅ is —Si (CH ₃ ) ₃ , or substituted by -Si(CH ₃ ) ₃ .

More specifically, for example, the above compound may be any one selected from the following compounds:

The compound represented by Formula 1 and the compound comprising the structural unit represented by Formula 1 each have at least one substituted or unsubstituted silyl group, or have a substituent substituted with at least one silyl group. Therefore, in an organic light-emitting device using the compound, particularly a blue thermally activated delayed fluorescence (TADF) device and a blue fluorescent device, compared with an organic light-emitting device using a compound having no silyl substituent, improved quantum efficiency.

Meanwhile, the compound represented by Formula 1 can be produced, for example, by the production method shown in Reaction Scheme 1 below. The preparation method can be further specified in the preparation examples described later.

[Reaction Scheme 1]

In Reaction Scheme 1, A ₁ to A ₃ are as defined in Formula 1, R is as defined in Formula 1 for Ra _, R _b and R ₁ to R ₃ , and Z means halogen or hydrogen.

The compound represented by Formula 1 can be prepared by appropriately substituting the starting material according to the structure of the compound to be prepared with reference to Reaction Scheme 1.

Meanwhile, the present invention provides an organic light emitting device including the compound represented by Formula 1. In one example, the present invention provides an organic light-emitting device, which includes: a first electrode; a second electrode disposed on the side opposite to the first electrode; and at least one electrode disposed between the first electrode and the second electrode. organic material layers, wherein at least one of the organic material layers contains the compound represented by Formula 1.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, or it may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer. However, the structure of the organic light emitting device is not limited thereto, and it may include a smaller number of organic layers.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but it may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including, in addition to the light-emitting layer as the organic material layer, a hole injection layer and a hole transport layer between the first electrode and the light-emitting layer, and The electron transport layer and the electron injection layer between the layer and the second electrode. However, the structure of the organic light emitting device is not limited thereto, and it may include a lesser or greater number of organic layers.

In addition, the organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, at least one organic material layer, and a cathode are sequentially stacked on a substrate. In addition, the organic light emitting device according to the present invention may be an inverted organic light emitting device in which a cathode, at least one organic material layer, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light emitting device according to an embodiment of the present invention is shown in FIGS. 1 and 2 .

FIG. 1 shows an example of an organic light emitting device including a substrate 1 , an anode 2 , a light emitting layer 3 and a cathode 4 . In such a structure, the compound represented by Formula 1 may be included in the light emitting layer.

FIG. 2 shows an example of an organic light emitting device including a substrate 1 , an anode 2 , a hole injection layer 5 , a hole transport layer 6 , a light emitting layer 7 , an electron transport layer 8 and a cathode 4 . In such a structure, the compound represented by Formula 1 may be contained in at least one layer of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer, and it is preferably contained in the light emitting layer.

The organic light emitting device according to the present invention may be manufactured by materials and methods known in the art except that at least one of the organic material layers contains the compound represented by Formula 1. Also, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

For example, an organic light emitting device according to the present invention may be fabricated by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light-emitting device can be manufactured by depositing a metal, a metal oxide having conductivity, on a substrate by using a PVD (Physical Vapor Deposition) method such as sputtering or electron beam evaporation , or an alloy thereof to form an anode, an organic material layer including a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer is formed on the anode, and then a material that can be used as a cathode is deposited on the organic material layer. In addition to such methods, organic light emitting devices can also be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In particular, the compound represented by Formula 1 may be contained in the light-emitting layer, and the light-emitting layer is produced not by a solution coating method including an organic solvent but by a vacuum deposition method, thereby enabling improved efficiency and low driving voltage, and/or improve lifetime characteristics.

In addition to such methods, an organic light emitting device can be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (International Publication WO 2003/012890). However, the manufacturing method is not limited thereto.

For example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

As the anode material, it is generally preferable to use a material having a large work function so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material include: metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide ( IZO); combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; conducting polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-bis oxy)thiophene] (PEDOT), polypyrrole, polyaniline; etc., but not limited thereto.

As a cathode material, it is generally preferable to use a material having a small work function so that electrons can be easily injected into the organic material layer. Specific examples of cathode materials include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structure materials such as LiF/Al or LiO ₂ /Al; etc., but not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes, has an effect of injecting holes in the anode, and acts on the light emitting layer or The light-emitting material has an excellent hole injection effect, prevents excitons generated in the light-emitting layer from moving to the electron injection layer or electron injection material, and has excellent film-forming ability. Preferably the HOMO (Highest Occupied Molecular Orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include compounds represented by Formula 1 according to the present invention, or metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanitrilehexaazatriphenylene-based organic materials, Quinacridone-based organic materials, perylene-based organic materials, anthraquinone, polyaniline, polythiophene-based conductive polymers, etc., but not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. The hole transport material is suitably a material having a large hole mobility that can receive holes from the anode or the hole injection layer and transfer the holes to the light emitting layer. Specific examples thereof include arylamine-based organic materials, conductive polymers, block copolymers in which both conjugated and non-conjugated portions exist, and the like, but are not limited thereto.

唑、基于苯并噻唑和基于苯并咪唑的化合物；基于聚(对亚苯基亚乙烯基)(PPV)的聚合物；螺环化合物；和聚芴；红荧烯；等等，但不限于此。A light-emitting material is a material capable of emitting light in a visible light region by combining holes and electrons respectively transported from a hole transport layer and an electron transport layer, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include: 8-hydroxy-quinoline aluminum complexes (Alq ₃ ); carbazole-based compounds; dipolystyryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds;

Azole, benzothiazole-based, and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; and polyfluorenes; rubrene; and the like, but not limited to this.

The light emitting layer may contain a host material and a dopant material as described above. The compound represented by Formula 1 may be a dopant material, and the content of the dopant material may be 0.5% by weight to 20% by weight relative to the total content of the light emitting layer.

The host material may also include fused aromatic ring derivatives, heterocyclic ring-containing compounds, and the like. Specifically, the host material is preferably a compound represented by Formula 3 below.

[Formula 3]

In Equation 3,

Ar is a C _6-20 aryl group or a C _2-60 heteroaryl group comprising at least one heteroatom selected from N, O and S, and

n may be an integer of 1 to 10.

The compound represented by Formula 3 may be a compound represented by Formula 4 below.

[Formula 4]

In Equation 4,

Ar ₁ to Ar ₄ are each independently a C _6-20 aryl group or a C _2-60 heteroaryl group comprising at least one heteroatom selected from N, O and S,

X can be a compound selected from:

基、三亚苯基、芘基、二苯并呋喃基、二苯并噻吩基、咔唑基、苯并咔唑基或苯基取代的咔唑基，以及Wherein R _{and R} are each independently hydrogen, phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthrenyl, fluorenyl, benzofluorenyl,

radical, triphenylene, pyrenyl, dibenzofuryl, dibenzothienyl, carbazolyl, benzocarbazolyl or phenyl substituted carbazolyl, and

基、三亚苯基、芘基、咔唑基或苯基取代的咔唑基。Ar ₅ is phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, fluorenyl,

group, triphenylene, pyrenyl, carbazolyl or phenyl substituted carbazolyl.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer, and the electron transport material is a material that can well receive electrons from the cathode and transport electrons to the light-emitting layer, and has a large electron transfer rate material is suitable. Specific examples thereof include: 8-hydroxyquinoline Al complexes; complexes including Alq ₃ ; organic radical compounds; hydroxyflavone-metal complexes; and the like, but are not limited thereto. The electron transport layer can be used together with the previously desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are common materials with a small work function followed by a layer of aluminum or silver. Specific examples thereof include cesium, barium, calcium, ytterbium and samarium, and in each case are followed by a layer of aluminum or silver.

唑、

二唑、三唑、咪唑、苝四羧酸、亚芴基甲烷、蒽酮等及其衍生物；金属配合物化合物；含氮5元环衍生物；等等，但不限于此。The electron injection layer is a layer that injects electrons from an electrode, and is preferably a compound that has the ability to transport electrons, has an effect of injecting electrons from a cathode, and has an excellent electron injection effect on a light-emitting layer or a light-emitting material, preventing light emission The excitons generated in the layer move to the hole injection layer, and have excellent thin film forming ability. Specific examples thereof include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide,

azole,

Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, etc., and their derivatives; metal complex compounds; nitrogen-containing 5-membered ring derivatives; etc., but not limited thereto.

Examples of metal complex compounds include lithium 8-quinolinate, zinc bis(8-quinolinate), copper bis(8-quinolinate), manganese bis(8-quinolinate), tris(8-quinolinate) tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxyquinoline) And [h] quinoline) zinc, bis (2-methyl-8-quinoline) gallium chloride, bis (2-methyl-8-quinoline) (o-cresol) gallium, bis (2-methyl- 8-quinoline)(1-naphthol)aluminum, bis(2-methyl-8-quinoline)(2-naphthol)gallium, etc., but not limited thereto.

The organic light emitting device according to the present invention may be a front-side emission type, a back-side emission type, or a double-side emission type according to materials used.

In addition, the compound represented by Formula 1 may be contained in an organic solar cell or an organic transistor in addition to an organic light emitting device.

Preparation of the compound represented by Formula 1 and an organic light emitting device including the same will be described in detail in the following examples. However, these examples are presented for illustrative purposes only, and the scope of the present invention is not limited thereto.

Embodiment 1: the synthesis of formula 1

(1-a) Synthesis of Intermediate 1-A

Will contain 1-bromo-2,3-dichlorobenzene (22.6g), bis(4-(tert-butyl)phenyl)amine (58.0g), Pd(PtBu ₃ ) ₂ (0.5g), NaOtBu (25.0 A flask of g) and xylene (260ml) was heated to 130°C and stirred for 4 hours. The reaction solution was cooled to room temperature, and water and ethyl acetate were added to separate a liquid layer. Then the solvent was distilled off under reduced pressure. This was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=50%/50% (vol/vol)) to obtain Intermediate 1-A (20.4 g). The mass spectrum of the solid was measured, and as a result, a peak at M/Z=671 was confirmed.

(1-b) Synthesis of Intermediate 1-B

A 1.7M tert-butyllithium pentane solution (9.2 ml) was added to a flask containing Intermediate 1-A (10.0 g) and tert-butylbenzene (160 ml) at 0° C. under an argon atmosphere. After the dropwise addition was completed, the temperature was raised to 70° C., and the mixture was stirred for 4 hours to distill off pentane. After cooling to -40°C, boron tribromide (1.6 ml) was added thereto, and the mixture was warmed up to room temperature and stirred for 4 hours. Thereafter, the mixture was cooled to 0°C again, and N,N-diisopropylethylamine (6.6 ml) was added thereto and stirred at room temperature, and then stirred at 80°C for 4 hours. The reaction solution was cooled to room temperature, and water and ethyl acetate were added thereto to separate a liquid layer. Then the solvent was distilled off under reduced pressure. Acetonitrile was added thereto to obtain Intermediate 1-B (2.8 g). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=645 was confirmed.

(1-c) Synthesis of intermediate 1-C

Intermediate 1-B (4.0 g) was dissolved in 300 ml of chloroform, and N-bromosuccinimide (1.2 g) was added thereto over 30 minutes, followed by stirring at room temperature for 4 hours. Distilled water was added to the reaction solution to complete the reaction, and the organic layer was extracted. The reaction solution was concentrated, and Compound 1-C (2.0 g) was obtained using column chromatography (developing solvent: hexane/ethyl acetate=50%/50% (vol/vol)). The peak was determined to be at M/Z=724.

(1-d) Synthesis of compound 1

Intermediate 1-C (2.0 g) was dissolved in 200 ml of anhydrous tetrahydrofuran under a nitrogen atmosphere, and the ambient temperature of the reactor was maintained at -78°C. Then, 1.1 ml of 2.5M-butyllithium was slowly added dropwise. After completion of the dropwise addition, stirring was performed for 1 hour, 0.6 ml of trimethylchlorosilane was dissolved in 20 ml of purified tetrahydrofuran, and then slowly added dropwise. The reaction solution was stirred for about 1 hour while being kept at -78°C, and dilute hydrochloric acid was then added to the reaction solution to complete the reaction. The liquid layer was separated and extracted with dichloromethane. The resulting organic layer was dried over magnesium sulfate, filtered, and then distilled under reduced pressure. Column chromatography (developing solvent: hexane/ethyl acetate=50%/50% (vol/vol)) was used to prepare Compound 1 (0.4 g). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=717 was confirmed.

Compound 1 was measured using a spectrophotometer U-3310 (manufactured by Hitachi High-Tech Science Corporation), and an absorption peak wavelength of 437 nm was observed. Furthermore, Compound 1 was measured using a fluorescence spectrum measuring device, a fluorescence spectrophotometer F-7000 (manufactured by Hitachi High-Tech Science Corporation), and it was observed that the phosphor luminescence peak wavelength was 452 nm. Fig. 3 is a graph measuring the absorption peak wavelength of Compound 1 by spectrofluorometry.

In addition, the half-value width was measured using a fluorescence spectrophotometer F-7000 (manufactured by Hitachi High-Tech Science Corporation), and the measurement method was as follows. Specifically, Compound 1 was dissolved in a solvent (toluene) (sample 5 [μmol/mL]) and used as a sample for fluorescence measurement. A sample for fluorescence measurement placed in a quartz chamber is irradiated with excitation light at room temperature, and the fluorescence intensity is measured while changing the wavelength. In the emission spectrum, the vertical axis represents the fluorescence intensity, and the horizontal axis represents the wavelength. The half-value width was measured from this emission spectrum, and as a result, the half-value width of Compound 1 was 30 nm. Fig. 4 is a graph measuring the half-value width of Compound 1 by spectrofluorometry.

Embodiment 2: the synthesis of compound 2

Compound 2 (0.2 g) was prepared in the same manner as in Step 1-d for the synthesis of Compound 1, except that 0.6 ml of trimethylchlorosilane was changed to 0.8 ml of chloro(dimethyl)phenylsilane. The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=779 was confirmed.

Embodiment 3: the synthesis of compound 3

(3-a) Synthesis of Intermediate 3-A

A mixture containing 1-bromo-2,3-dichlorobenzene (22.6 g), bis(4-(tert-butyl)phenyl)amine (28.2 g), Pd(PtBu ₃ ) ₂ (0.2 g), NaOtBu (12.6 A flask of g) and toluene (130ml) was heated to 110°C and stirred for 4 hours. The reaction solution was cooled to room temperature, and water and ethyl acetate were added to separate a liquid layer. Then the solvent was distilled off under reduced pressure. This was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=50%/50% (vol/vol)) to obtain Intermediate 3-A (20.8 g). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=426 was confirmed.

(3-b) Synthesis of Intermediate 3-B

A flask containing Intermediate 3-A (41.1 g), xylylamine (20.6 g), Pd(PtBu ₃ ) ₂ (0.2 g), NaOtBu (12.6 g) and toluene (130 ml) was heated to 110° C. and Stir for 4 hours. The reaction solution was cooled to room temperature, and water and ethyl acetate were added to separate a liquid layer. Then the solvent was distilled off under reduced pressure. This was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=50%/50% (vol/vol)) to obtain Intermediate 3-B (19.2 g). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=587 was confirmed.

(3-c) Synthesis of Intermediate 3-C

Intermediate 3-C (3.0 g) was obtained in the same manner as in Step 1-b for the synthesis of Intermediate 1-B, except that Intermediate 1-A was changed to Intermediate 3-B (8.7 g ). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=561 was confirmed.

(3-d) Synthesis of intermediate 3-D

Intermediate 3-D (1.6 g) was obtained in the same manner as in step 1-c for the synthesis of Intermediate 1-C, except that Intermediate 1-B was changed to Intermediate 3-C (3.5 g ). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=639 was confirmed.

(3-e) Synthesis of compound 3

Compound 3 (0.3 g) was obtained in the same manner as in Step 1-d for the synthesis of Compound 1, except that Intermediate 1-C was changed to Intermediate 3-D (1.8 g). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=633 was confirmed.

Embodiment 4: the synthesis of compound 4

(4-a) Synthesis of Intermediate 4-A

Diisopropylamine (15.5ml) was added to 200ml of anhydrous tetrahydrofuran under a nitrogen atmosphere, and then 42.0ml of 2.5M-butyllithium was slowly added dropwise at -78°C. The reaction solution was stirred for about 2 hours while maintaining at -78°C. 49.4 g of (3,5-dibromophenyl)triphenylsilane was dissolved in 100 ml of tetrahydrofuran, and slowly added dropwise. After stirring at -78°C for 2 hours, excess carbon dioxide gas was added and the temperature was gradually raised to room temperature. Dilute hydrochloric acid was added to the reaction solution to complete the reaction, and then the liquid layer was separated and extracted with dichloromethane. The resulting organic layer was dried over magnesium sulfate, filtered, and then distilled under reduced pressure. Column chromatography (developing solvent: hexane/ethyl acetate=60%/40% (vol/vol)) was used to prepare 34.2 g of 2,6-dibromo-4-(triphenylsilyl)benzoic acid.

Subsequently, 34.2 g of 2,6-dibromo-4-(triphenylsilyl)benzoic acid were dissolved in 160 ml of sulfuric acid and heated at 60° C. for 2 hours. After cooling to room temperature, sodium azide (NaN ₃ ) (8.2 g) was added, and stirred at 0° C. for 48 hours. After the reaction was completed, the liquid layer was separated and extracted with ammonia and ethyl acetate. The resulting organic layer was dried over magnesium sulfate, filtered, and then distilled under reduced pressure. Column chromatography (developing solvent: ethyl acetate) was used to prepare 22.6 g of 2,6-dibromo-4-(triphenylsilyl)aniline.

Subsequently, 2,6-dibromo-4-(triphenylsilyl)aniline (22.6 g) was suspended in an aqueous sulfuric acid solution, and 6.0 g of sodium nitrite was added at 0° C. for diazotization. Thereafter, an aqueous urea solution was added. This solution was added to an aqueous hydrochloric acid solution of CuCl ₂ (13.1 g) in multiple additions, and stirred at room temperature for 2 hours and at 60° C. for 4 hours. After the reaction was completed, the liquid layer was separated and extracted with ammonia and ethyl acetate. The resulting organic layer was dried over magnesium sulfate, filtered, and distilled under reduced pressure. The precipitated solid was washed with water and ethanol and dried to obtain Intermediate 4-A (10.6 g). The mass spectrum of the obtained solid was measured, and as a result, it was confirmed that the peak was at M/Z=529.

(4-b) Synthesis of Intermediate 4-B

Intermediate 4-B (36.0 g) was obtained in the same manner as in Step 1-a for the synthesis of Intermediate 1-A, except that 1-bromo-2,3-dichlorobenzene (22.6 g) Changed to Intermediate 4-A (52.9 g). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=930 was confirmed.

(4-c) Synthesis of Compound 4

Compound 4 (1.2 g) was obtained in the same manner as in Step 1-b for the synthesis of Intermediate 1-B, except that Intermediate 1-A was changed to Intermediate 4-B (13.8 g). The mass spectrum of the obtained solid was measured, and as a result, it was confirmed that the peak was at M/Z=903.

Embodiment 5: the synthesis of compound 5

(5-a) Synthesis of Intermediate 5-A

Compound 5-A (29.0 g) was obtained in the same manner as in step 4-b for the synthesis of intermediate 4-B, except that bis(4-(tert-butyl)phenyl)amine (58.0 g ) was changed to di-p-tolylamine (40.7 g). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=761 was confirmed.

(5-b) Synthesis of Compound 5

Compound 5 (1.8 g) was obtained in the same manner as in Step 4-c for the synthesis of Compound 4, except that Intermediate 4-B (13.8 g) was changed to Intermediate 5-A (11.3 g). The mass spectrum of the obtained solid was measured, and as a result, it was confirmed that the peak was at M/Z=735.

Embodiment 6: the synthesis of compound 6

(6-a) Synthesis of Intermediate 6-A

A flask containing Intermediate 4-A (26.4g), N-phenylnaphthalen-1-amine (24.0g), Pd( _PtBu3 ) ₂ (0.4g), NaOtBu (13.0g) and xylene (260ml) Heat to 130°C and stir for 4 hours. The reaction solution was cooled to room temperature, and water and ethyl acetate were added to separate a liquid layer. Then the solvent was distilled off under reduced pressure. This was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=50%/50% (vol/vol)) to obtain Intermediate 6-A (12.8 g). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=805 was confirmed.

(6-b) Synthesis of Compound 6

Compound 6 (2.0 g) was obtained in the same manner as in Step 4-c for the synthesis of Compound 4, except that Intermediate 4-B (13.8 g) was changed to Intermediate 6-A (12.0 g). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=779 was confirmed.

Embodiment 7: the synthesis of compound 7

(7-a) Synthesis of Intermediate 7-A

Intermediate 7-A (10.6 g) was obtained in the same manner as in step 6-a for the synthesis of compound 6-A, except that N-phenylnaphthalene-1-amine (24.0 g) was changed to N -(m-Tolyl)naphthalen-1-amine (25.5 g). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=834 was confirmed.

(7-b) Synthesis of Compound 7

Compound 7 (2.2 g) was obtained in the same manner as in Step 4-c for the synthesis of Compound 4, except that Intermediate 4-B (13.8 g) was changed to Intermediate 7-A (12.4 g). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=807 was confirmed.

Embodiment 8: the synthesis of compound 8

(8-a) Synthesis of Intermediate 8-A

Diisopropylamine (15.5ml) was added to 200ml of anhydrous tetrahydrofuran under a nitrogen atmosphere, and then 42.0ml of 2.5M-butyllithium was slowly added dropwise at -78°C. The reaction solution was stirred for about 2 hours while being kept at -78°C, and 37.0 g of (3,5-dibromophenyl)dimethyl(phenyl)silane was dissolved in 100 ml of tetrahydrofuran and slowly added dropwise. After stirring at -78°C for 2 hours, excess carbon dioxide gas was added, and the temperature was gradually raised to room temperature. Dilute hydrochloric acid was added to the reaction solution to complete the reaction, and then the liquid layer was separated and extracted with dichloromethane. The resulting organic layer was dried over magnesium sulfate, filtered, and distilled under reduced pressure. Use column chromatography (developing solvent: hexane/ethyl acetate=60%/40% (volume/volume)) to prepare 28.2g 2,6-dibromo-4-(dimethyl(phenyl)silyl )benzoic acid.

Subsequently, 26.3 g of 2,6-dibromo-4-(dimethyl(phenyl)silyl)benzoic acid was dissolved in 160 ml of sulfuric acid and heated at 60° C. for 2 hours. After cooling to room temperature, sodium azide (NaN ₃ ) (8.2 g) was added, and stirred at 0° C. for 48 hours. After the reaction was completed, the liquid layer was separated and extracted with ammonia and ethyl acetate. The resulting organic layer was dried over magnesium sulfate, filtered, and then distilled under reduced pressure. Column chromatography (developing solvent: ethyl acetate) was used to prepare 16.6 g of 2,6-dibromo-4-(dimethyl(phenyl)silyl)aniline.

Subsequently, 2,6-dibromo-4-(dimethyl(phenyl)silyl)aniline (17.1 g) was suspended in an aqueous sulfuric acid solution, and 6.0 g of sodium nitrite was added at 0°C for diazo change. Thereafter, an aqueous urea solution was added. This solution was added to an aqueous hydrochloric acid solution of CuCl ₂ (13.1 g) in multiple additions, and stirred at room temperature for 2 hours and at 60° C. for 4 hours. After the reaction was completed, the liquid layer was separated and extracted with ammonia and ethyl acetate. The resulting organic layer was dried over magnesium sulfate, filtered, and distilled under reduced pressure. The precipitated solid was washed with water and ethanol and dried to obtain Intermediate 8-A (6.8 g). The mass spectrum of the obtained solid was measured, and as a result, it was confirmed that the peak was at M/Z=405.

(8-b) Synthesis of Intermediate 8-B

A mixture containing Intermediate 8-A (10.1 g), bis(4-(tert-butyl)phenyl)amine (14.5 g), Pd(PtBu ₃ ) ₂ (0.2 g), NaOtBu (6.2 g) and xylene ( 70ml) flask was heated to 130°C and stirred for 4 hours. The reaction solution was cooled to room temperature, and water and ethyl acetate were added to separate a liquid layer. Then the solvent was distilled off under reduced pressure. Silica gel column chromatography (developing solvent: hexane/ethyl acetate=50%/50% (vol/vol)) was used to prepare Intermediate 8-B (5.0 g). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=792 was confirmed.

(8-c) Synthesis of Compound 8

Compound 8 (1.7 g) was obtained in the same manner as in Step 4-c for the synthesis of Compound 4, except that Intermediate 4-B (13.8 g) was changed to Intermediate 8-B (11.7 g). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=779 was confirmed.

Embodiment 9: the synthesis of compound 9

(9-a) Synthesis of Intermediate 9-A

Intermediate 9-A (4.2 g) was obtained in the same manner as in Step 8-b for the synthesis of Intermediate 8-B, except that bis(4-(tert-butyl)phenyl)amine (14.5 g) was changed to diphenylamine (8.7 g). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=581 was confirmed.

(9-b) Synthesis of compound 9

Compound 9 (1.0 g) was obtained in the same manner as in Step 4-c for the synthesis of Compound 4, except that Intermediate 4-B (13.8 g) was changed to Intermediate 9-A (8.6 g). The mass spectrum of the obtained solid was measured, and as a result, it was confirmed that the peak was at M/Z=555.

Embodiment 10: the synthesis of compound 10

(10-a) Synthesis of Intermediate 10-A

Intermediate 10-A (4.6 g) was obtained in the same manner as in Step 8-b for the synthesis of Intermediate 8-B, except that bis(4-(tert-butyl)phenyl)amine (14.5 g) Change to N-phenylnaphthalen-1-amine (11.3 g). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=681 was confirmed.

(10-b) Synthesis of Compound 10

Compound 10 (1.2 g) was obtained in the same manner as in Step 4-c for the synthesis of Compound 4, except that Intermediate 4-B (13.8 g) was changed to Intermediate 10-A (10.1 g). The mass spectrum of the obtained solid was measured, and as a result, it was confirmed that the peak was at M/Z=655.

Embodiment 11: the synthesis of compound 11

(11-a) Synthesis of Intermediate 11-A

will contain 1,3-dibromo-2-chloro-5-methoxybenzene (7.5g), diphenylamine (8.9g), Pd(PtBu ₃ ) ₂ (0.2g), NaOtBu (6.2g) and xylene (60ml) flask was heated to 130°C and stirred for 4 hours. The reaction solution was cooled to room temperature, and water and ethyl acetate were added to separate a liquid layer. Then the solvent was distilled off under reduced pressure. This was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=50%/50% (vol/vol)) to prepare Intermediate 11-A (3.2 g). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=477 was confirmed.

(11-b) Synthesis of Intermediate 11-B

Intermediate 11-B (2.0 g) was obtained in the same manner as in step 4-c for the synthesis of compound 4, except that intermediate 4-B (13.8 g) was changed to intermediate 11-A (7.1 g). The mass spectrum of the obtained solid was measured, and as a result, it was confirmed that the peak was at M/Z=450.

(11-c) Synthesis of Intermediate 11-C

To a flask containing Intermediate 11-B (4.4 g) and chloroform (100 ml) was added boron tribromide (1.0 ml) at room temperature under a nitrogen atmosphere, and the mixture was stirred at room temperature for 48 hours. Thereafter, the reaction solution was distilled off, an aqueous sodium bicarbonate solution (200 ml) was added, and the liquid layer was separated with chloroform. The solvent was distilled off under reduced pressure to obtain Intermediate 11-C (2.8 g). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=436 was confirmed.

(11-d) Synthesis of Intermediate 11-D

Intermediate 11-C (2.8 g), nonafluorobutane-1-sulfonyl fluoride (2.2 g) and potassium carbonate (1.5 g) were dissolved in acetonitrile (40 ml), heated to 50° C., and stirred for 4 hours. After cooling to room temperature, distilled water was added to remove potassium carbonate. Thus, Intermediate 11-D (1.4 g) was obtained.

(11-e) Synthesis of compound 11

Intermediate 11-D (2.4 g), (4-(trimethylsilyl)phenyl)boronic acid (0.8 g) and potassium carbonate (1.4 g) were dissolved in 20 ml of tetrahydrofuran and 10 ml of distilled water, and thereto was added Tetrakis(triphenylphosphine)palladium (0.2 g), then refluxed for 12 hours. After cooling to room temperature, the aqueous layer was removed, and magnesium sulfate was added to the organic layer, followed by filtration. After concentration, acetonitrile was added to obtain compound 11 (0.6 g). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=569 was confirmed.

Embodiment 12: the synthesis of compound 12

Intermediate 11-D (2.4 g) was dissolved in 24 ml anhydrous THF under nitrogen atmosphere, and the ambient temperature of the reactor was maintained at -78°C. Then, 1.4 ml of 2.5M-butyllithium was slowly added dropwise. After completion of the dropwise addition, stirring was performed for 1 hour, and 0.7 ml of trimethylchlorosilane was dissolved in 10 ml of purified tetrahydrofuran, followed by slow dropwise addition. The reaction solution was stirred for about 1 hour while being kept at -78°C, and then dilute hydrochloric acid was added to the reaction solution to complete the reaction, and then the liquid was separated using dichloromethane. The resulting organic layer was dried over magnesium sulfate, filtered, and then distilled under reduced pressure. Column chromatography (developing solvent: hexane/ethyl acetate=50%/50% (vol/vol)) was used to prepare Compound 12 (0.4 g). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=493 was confirmed.

Embodiment 13: the synthesis of compound 13

(13-a) Synthesis of Intermediate 13-A

Intermediate 13-A (4.0 g) was obtained in the same manner as in step 11-a for the synthesis of compound 11-A, except that diphenylamine (8.9 g) was changed to N-phenylnaphthalene-1- Amine (11.5 g). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=577 was confirmed.

(13-b) Synthesis of Intermediate 13-B

Intermediate 13-B (13.0 g) was obtained in the same manner as in step 4-c for the synthesis of compound 4, except that intermediate 4-B (13.8 g) was changed to intermediate 13-A (8.6 g). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=550 was confirmed.

(13-c) Synthesis of Intermediate 13-C

To a flask containing Intermediate 13-B (5.4 g) and chloroform (100 ml) was added boron tribromide (1.0 ml) at room temperature under a nitrogen atmosphere, and the mixture was stirred at room temperature for 48 hours. Thereafter, the reaction solution was distilled off, an aqueous sodium bicarbonate solution (200 ml) was added, and the liquid layer was separated with chloroform. The solvent was distilled off under reduced pressure to obtain Intermediate 13-C (2.8 g). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=536 was confirmed.

(13-d) Synthesis of Intermediate 13-D

Intermediate 13-C (3.4 g), nonafluorobutane-1-sulfonyl fluoride (2.2 g) and potassium carbonate (1.5 g) were dissolved in acetonitrile (40 ml), heated to 50° C., and stirred for 4 hours. After cooling to room temperature, distilled water was added to remove potassium carbonate. Thus, Intermediate 13-D (1.6 g) was obtained.

(13-e) Synthesis of compound 13

Intermediate 13-D (2.7 g), (4-(trimethylsilyl)phenyl)boronic acid (0.8 g) and potassium carbonate (1.4 g) were dissolved in 20 ml of tetrahydrofuran and 10 ml of distilled water, and thereto was added Tetrakis(triphenylphosphine)palladium (0.2 g), then refluxed for 12 hours. After cooling to room temperature, the aqueous layer was removed, and magnesium sulfate was added to the organic layer, followed by filtration. After concentration, acetonitrile was added to obtain compound 13 (0.8 g). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=669 was confirmed.

Embodiment 14: the synthesis of compound 14

Intermediate 13-D (2.7 g) was dissolved in anhydrous tetrahydrofuran (24 ml) under a nitrogen atmosphere, and the ambient temperature of the reactor was maintained at -78°C. Then, 1.4 ml of 2.5M-butyllithium was slowly added dropwise. After completion of the dropwise addition, stirring was performed for 1 hour, and then 0.7 ml of trimethylchlorosilane was dissolved in 10 ml of purified tetrahydrofuran, followed by slow dropwise addition. The reaction solution was stirred for about 1 hour while maintaining at -78°C. Dilute hydrochloric acid was added to the reaction solution to complete the reaction, and then the liquid was separated using dichloromethane. The resulting organic layer was dried over magnesium sulfate, filtered, and then distilled under reduced pressure. Column chromatography (developing solvent: hexane/ethyl acetate=50%/50% (vol/vol)) was used to prepare Compound 14 (0.6 g). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=593 was confirmed.

Embodiment 15: the synthesis of compound 15

(15-a) Synthesis of Intermediate 15-A

1,3-Dibromonaphthalene-2-amine (13.5 g) was suspended in an aqueous sulfuric acid solution, and 6.0 g of an aqueous sodium nitrite solution was added at 0° C. for diazotization. Thereafter, an aqueous urea solution was added. This solution was added to an aqueous hydrochloric acid solution of CuCl ₂ (13.1 g) in multiple additions, and stirred at room temperature for 2 hours and at 60° C. for 4 hours. After the reaction was completed, the liquid layer was separated and extracted with ammonia and ethyl acetate. The resulting organic layer was dried over magnesium sulfate, filtered, and distilled under reduced pressure. The precipitated solid was washed with water and ethanol and dried to obtain Intermediate 15-A (5.4 g). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=320 was confirmed.

(15-b) Synthesis of Intermediate 15-B

A mixture containing Intermediate 15-A (8.0 g), bis(4-(trimethylsilyl)phenyl)amine (16.4 g), Pd(PtBu ₃ ) ₂ (0.2 g), NaOtBu (6.2 g) and A flask of xylene (60ml) was heated to 130°C and stirred for 4 hours. The reaction solution was cooled to room temperature, and water and ethyl acetate were added to separate a liquid layer. Then the solvent was distilled off under reduced pressure. This was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=50%/50% (vol/vol)) to obtain Intermediate 15-B (4.8 g). The mass spectrum of the solid was measured, and as a result, a peak at M/Z=786 was confirmed.

(15-c) Synthesis of compound 15

Compound 15 (3.0 g) was obtained in the same manner as in Step 4-c for the synthesis of Compound 4, except that Intermediate 4-B (13.8 g) was changed to Intermediate 15-B (11.7 g). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=759 was confirmed.

Embodiment 16: the synthesis of compound 16

(16-a) Synthesis of Intermediate 16-A

Containing intermediate 3-A (41.1 g), bis(4-(trimethylsilyl)phenyl)amine (31.7 g), Pd(PtBu ₃ ) ₂ (0.2 g), NaOtBu (12.6 g) and di A flask of toluene (130ml) was heated to 110°C and stirred for 4 hours. The reaction solution was cooled to room temperature, and water and ethyl acetate were added to separate a liquid layer. Then the solvent was distilled off under reduced pressure. This was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=50%/50% (vol/vol)) to obtain Intermediate 16-A (19.8 g). The mass spectrum of the solid was measured, and as a result, a peak at M/Z=704 was confirmed.

(16-b) Synthesis of compound 16

Compound 16 (3.0 g) was obtained in the same manner as in Step 4-b for the synthesis of Compound 4, except that Intermediate 4-B (13.8 g) was changed to Intermediate 16-A (11.2 g). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=677 was confirmed.

Embodiment 17: the synthesis of compound 17

(17-a) Synthesis of Intermediate 17-A

A mixture containing 1-bromo-2,3-dichloro-5-methylbenzene (9.3g), diphenylamine (6.9g), Pd(PtBu ₃ ) ₂ (0.2g), NaOtBu (6.2g) and toluene (90ml ) flask was heated to 110°C and stirred for 4 hours. The reaction solution was cooled to room temperature, and water and ethyl acetate were added to separate a liquid layer. Then the solvent was distilled off under reduced pressure. This was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=50%/50% (vol/vol)) to obtain Intermediate 17-A (4.0 g). The mass spectrum of the solid was measured, and as a result, a peak at M/Z=328 was confirmed.

(17-b) Synthesis of Intermediate 17-B

A mixture containing Intermediate 17-A (6.6 g), bis(4-(trimethylsilyl)phenyl)amine (6.9 g), Pd(PtBu ₃ ) ₂ (0.2 g), NaOtBu (6.2 g) and A flask of xylene (90ml) was heated to 130°C and stirred for 8 hours. The reaction solution was cooled to room temperature, and water and ethyl acetate were added to separate a liquid layer. Then the solvent was distilled off under reduced pressure. This was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=50%/50% (vol/vol)) to obtain Intermediate 17-B (2.8 g). The mass spectrum of the solid was measured, and as a result, it was confirmed that the peak was at M/Z=605.

(17-c) Synthesis of compound 17

Compound 17 (1.4 g) was obtained in the same manner as in Step 4-c for the synthesis of Compound 4, except that Intermediate 4-B (13.8 g) was changed to Intermediate 17-B (9.0 g). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=579 was confirmed.

Embodiment 18: the synthesis of compound 18

(18-a) Synthesis of Intermediate 18-A

Diisopropylamine (15.5ml) was added to 200ml of anhydrous tetrahydrofuran under a nitrogen atmosphere, and then 42.0ml of 2.5M-butyllithium was slowly added dropwise at -78°C. The reaction solution was stirred for about 2 hours while being kept at -78°C, and 43.2 g of (3,5-dibromophenyl)(methyl)diphenylsilane was dissolved in 160 ml of tetrahydrofuran and slowly added dropwise. After stirring at -78°C for 2 hours, excess carbon dioxide gas was added, and the temperature was gradually raised to room temperature. Dilute hydrochloric acid was added to the reaction solution to complete the reaction, and then the liquid layer was separated and extracted with dichloromethane. The resulting organic layer was dried over magnesium sulfate, filtered, and then distilled under reduced pressure. Use column chromatography (developing solvent: hexane/ethyl acetate=60%/40% (volume/volume)) to prepare 29.0g 2,6-dibromo-4-(methyldiphenylsilyl)benzene formic acid.

Subsequently, 30.2 g of 2,6-dibromo-4-(methyldiphenylsilyl)benzoic acid were dissolved in 160 ml of sulfuric acid and heated at 60° C. for 2 hours. After cooling to room temperature, sodium azide (NaN ₃ ) (8.2 g) was added thereto, and stirred at 0° C. for 48 hours. After the reaction was completed, the liquid layer was separated and extracted with ammonia and ethyl acetate. The resulting organic layer was dried over magnesium sulfate, filtered, and then distilled under reduced pressure. Column chromatography (developing solvent: ethyl acetate) was used to prepare 14.6 g of 2,6-dibromo-4-(methyldiphenylsilyl)aniline.

Subsequently, 2,6-dibromo-4-(methyldiphenylsilyl)aniline (19.9 g) was suspended in an aqueous sulfuric acid solution, and 6.0 g of sodium nitrite was added at 0° C. for diazotization. Thereafter, an aqueous urea solution was added. This solution was added to an aqueous hydrochloric acid solution of CuCl ₂ (13.1 g) in multiple additions, and stirred at room temperature for 2 hours and at 60° C. for 4 hours. After the reaction was completed, the liquid layer was separated and extracted with ammonia and ethyl acetate. The resulting organic layer was dried over magnesium sulfate, filtered, and distilled under reduced pressure. The precipitated solid was washed with water and ethanol and dried to obtain Intermediate 18-A (7.0 g). The mass spectrum of the obtained solid was measured, and as a result, it was confirmed that the peak was at M/Z=467.

(18-b) Synthesis of Intermediate 18-B

A flask containing Intermediate 18-A (11.6 g), diphenylamine (9.0 g), Pd(PtBu ₃ ) ₂ (0.2 g), NaOtBu (6.2 g) and xylene (70 ml) was heated to 130° C. and stirred for 4 Hour. The reaction solution was cooled to room temperature, and water and ethyl acetate were added to separate a liquid layer. Then the solvent was distilled off under reduced pressure. This was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=50%/50% (vol/vol)) to obtain Intermediate 18-B (4.0 g). The mass spectrum of the solid was measured, and as a result, a peak at M/Z=643 was confirmed.

(18-c) Synthesis of compound 18

Compound 18 (1.2 g) was obtained in the same manner as in Step 4-c for the synthesis of Compound 4, except that Intermediate 4-B (13.8 g) was changed to Intermediate 18-B (9.5 g). The mass spectrum of the obtained solid was measured, and as a result, a peak at M/Z=617 was confirmed.

Embodiment 19: the synthesis of compound 19

(19-a) Synthesis of Intermediate 19-A

A mixture containing (3,5-dibromo-4-chlorophenyl)(methyl)diphenylsilane (11.6 g), 7-methyl-N-phenyldibenzo[b,d]furan-4- A flask of amine (14.4g), Pd( _PtBu3 ) ₂ (0.2g), NaOtBu (6.2g) and xylene (70ml) was heated to 130°C and stirred for 8 hours. The reaction solution was cooled to room temperature, and water and ethyl acetate were added to separate a liquid layer. Then the solvent was distilled off under reduced pressure. This was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=50%/50% (vol/vol)) to obtain Intermediate 19-A (4.8 g). The mass spectrum of the solid was measured, and as a result, a peak at M/Z=852 was confirmed.

(19-b) Synthesis of compound 19

Compound 19 (1.4 g) was obtained in the same manner as in Step 4-b for the synthesis of Compound 4, except that Intermediate 4-B (13.8 g) was changed to Intermediate 19-A (12.6 g). The mass spectrum of the obtained solid was measured, and as a result, it was confirmed that the peak was at M/Z=825.

Embodiment 20: the synthesis of compound 20

A mixture containing intermediate 11-D (1.8g), N-phenyl-4-(trimethylsilyl)aniline (0.7g), Pd(PtBu ₃ ) ₂ (0.1g), NaOtBu (3.8g) and A flask of toluene (20ml) was heated to 110°C and stirred for 4 hours. The reaction solution was cooled to room temperature, and water and ethyl acetate were added to separate a liquid layer. Then the solvent was distilled off under reduced pressure. This was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=50%/50% (vol/vol)) to obtain compound 20 (0.6 g). The mass spectrum of the solid was measured, and as a result, a peak at M/Z=660 was confirmed.

Experimental example 1

的ITO(氧化铟锡)薄膜的玻璃基底(Corning 7059玻璃)浸入其中溶解有清洁剂的蒸馏水中并通过超声波洗涤。所使用的清洁剂为从FisherCo.商购的产品，以及蒸馏水为通过使用从Millipore Co.商购的过滤器过滤两次的蒸馏水。将ITO洗涤30分钟，然后通过使用蒸馏水重复进行两次超声洗涤10分钟。在用蒸馏水洗涤完成之后，依次使用异丙醇、丙酮和甲醇溶剂进行超声波洗涤，并干燥所得产物。Apply it with a thickness of

A glass substrate (Corning 7059 glass) of an ITO (indium tin oxide) film was immersed in distilled water in which a detergent was dissolved and washed by ultrasonic waves. The detergent used was a product commercially available from Fisher Co., and the distilled water was distilled water filtered twice by using a filter commercially available from Millipore Co. The ITO was washed for 30 minutes, followed by two repetitions of ultrasonic washing for 10 minutes by using distilled water. After completion of washing with distilled water, ultrasonic washing was performed using isopropanol, acetone, and methanol solvents in sequence, and the resulting product was dried.

的厚度热真空沉积下式HAT的化合物以形成空穴注入层。在空穴注入层上以

的厚度真空沉积下式HT-A的化合物作为空穴传输层，然后真空沉积下式HT-B的化合物

以98:2的重量比真空沉积作为主体的化合物BH-1和作为掺杂剂的实施例1中制备的化合物1以形成厚度为

的发光层。On the prepared ITO transparent electrode with

A compound of the formula HAT is thermally vacuum deposited to form a hole injection layer. on the hole injection layer with

The thickness of vacuum deposition of the compound of the following formula HT-A as a hole transport layer, and then vacuum deposition of the compound of the following formula HT-B

With the weight ratio of 98:2, the compound BH-1 as the main body and the compound 1 prepared in the embodiment 1 as the dopant were vacuum-deposited to form a thickness of

the luminescent layer.

依次沉积厚度为

的掺杂有10重量％的银(Ag)的镁(Mg)和厚度为

的铝以形成阴极。从而，制造有机发光器件。Subsequently, the compound of the formula ET-A and the compound of the formula Liq are deposited in a ratio of 1:1 to a thickness of

The sequential deposition thickness is

of magnesium (Mg) doped with 10% by weight of silver (Ag) and a thickness of

aluminum to form the cathode. Thus, an organic light emitting device was manufactured.

/秒，将LiF的气相沉积速率保持在

/秒，并将铝的气相沉积速率保持在

/秒至

/秒。During the above process, the vapor deposition rate of the organic material was kept at

/sec, keep the vapor deposition rate of LiF at

/sec, and keep the vapor deposition rate of aluminum at

/sec to

/second.

Experimental Examples 2 to 22

An organic light-emitting device was fabricated in the same manner as in Experimental Example 1 except that the compounds shown in Table 1 below were used instead of Compound 1 in Experimental Example 1. In Table 1 below, BH-2 means the following compounds.

Comparative Experimental Examples 1 to 4

An organic light-emitting device was fabricated in the same manner as in Experimental Example 1 except that the compounds shown in Table 1 below were used instead of Compound 1 in Experimental Example 1. In Table 1 below, D-1 to D-4 mean the following compounds, respectively.

For the organic light-emitting devices manufactured in Experimental Examples 1 to 22 and Comparative Experimental Examples 1 to 4, the driving voltage, luminous efficiency, and color coordinates (CIEy) were measured at a current of 10 mA/cm ² , and measured at a current density of 20 mA/cm ² The time at which the luminance becomes 95% relative to the initial luminance (LT ₉₅ ) was measured below. The above results are shown in Table 1 below.

[Table 1]

As shown in Table 1, it was confirmed that Experimental Examples 1 to 22 exhibited excellent efficiency and lifetime compared with Comparative Experimental Examples 1 to 4. Specifically, when Experimental Examples 9, 11, and 12 were compared with Comparative Experimental Example 1, it was determined that Experimental Examples 9, 11 in which a silyl group was introduced, compared with Comparative Experimental Example 1 in which no silyl group was introduced, and 12 show a trend of about 30% increase in device lifetime. In addition, comparing Experimental Examples 6 and 14 with Comparative Experimental Example 2, Experimental Examples 6 and 14 in which a silyl group was introduced exhibited an increase in the lifetime of the device compared to Comparative Experimental Example 1 in which no silyl group was introduced About a 30% to 33% trend. It was confirmed that these tendencies were similarly exhibited between Experimental Example 15 and Comparative Experimental Example 3 and between Experimental Example 11 and Comparative Experimental Example 4. Therefore, in the case where a silyl group is attached to Formula 1 of the present invention, excellent heat resistance and decomposition resistance can be achieved. Therefore, it was confirmed that a device employing this compound, such as an organic light-emitting device, has high stability and a long lifetime when manufactured, stored and driven.

[Description of Reference Signs]

1: Substrate 2: Anode

3: Emitting layer 4: Cathode

5: Hole injection layer

6: Hole transport layer

7: Luminous layer

8: Electron transport layer

Claims (10)

1. A compound represented by the following formula 1:

[ formula 1]

Wherein, in the formula 1,

ring A ₁ To ring A ₃ Each independently a benzene ring, a naphthalene ring, a dibenzofuran ring or a dibenzothiophene ring,

R _a and R _b Each independently being unsubstituted or deuterated, C _1-10 Alkyl, tri (C) _1-10 Alkyl) silyl, tri (C) _6-20 Aryl) methylSilyl group, di (C) _1-10 Alkyl) (C) _6-20 Aryl) silyl or (C) _1-10 Alkyl) di (C) _6-20 Aryl) silyl substituted C _6-20 An aryl group, a heteroaryl group,

R ₁ to R ₃ Each independently is hydrogen; deuterium; unsubstituted tris (C) _1-10 Alkyl) silyl; unsubstituted tris (C) _6-20 Aryl) silyl; unsubstituted di (C) _1-10 Alkyl) (C _6-20 Aryl) silyl; unsubstituted (C) _1-10 Alkyl) di (C) _6-20 Aryl) silyl; unsubstituted or substituted by three (C) _1-10 Alkyl) silyl, tri (C) _6-20 Aryl) silyl, di (C) _1-10 Alkyl) (C _6-20 Aryl) silyl or (C) _1-10 Alkyl) di (C) _6-20 Aryl) silyl substituted di- (C) _6-20 Aryl) amino; unsubstituted C _1-10 An alkyl group; or unsubstituted or substituted by tri (C) _1-10 Alkyl) silyl, tri (C) _6-20 Aryl) silyl, di (C) _1-10 Alkyl) (C _6-20 Aryl) silyl or (C) _1-10 Alkyl) di (C) _6-20 Aryl) silyl substituted C _6-20 An aryl group, a heteroaryl group,

with the proviso that R _a 、R _b And R ₁ To R ₃ At least one of which is unsubstituted tri (C) _1-10 Alkyl) silyl, unsubstituted tri (C) _6-20 Aryl) silyl, unsubstituted di (C) _1-10 Alkyl) (C _6-20 Aryl) silyl or unsubstituted (C) _1-10 Alkyl) di (C) _6-20 Aryl) silyl groups, or by a tri (C) _1-10 Alkyl) silyl, tri (C) _6-20 Aryl) silyl, di (C) _1-10 Alkyl) (C _6-20 Aryl) silyl or (C) _1-10 Alkyl) di (C) _6-20 Aryl) silyl substitution, and

n1 to n3 are each independently an integer of 0 to 6.

2. The compound of claim 1, wherein the compound represented by formula 1 is represented by one of the following formulae 1-2, 1-4, 1-6, and 1-11 to 1-13:

[ formulas 1-2]

[ formulae 1 to 4]

[ formulae 1 to 6]

[ formulae 1 to 13]

Wherein, in the formulae 1-2, 1-4, 1-6 and 1-11 to 1-13,

X ₁ and X ₂ Each independently of the other is O or S,

R _a1 to R _a5 And R _b1 To R _b5 Each independently is hydrogen; deuterium; unsubstituted tris (C) _1-10 Alkyl) silyl groups; unsubstituted tris (C) _6-20 Aryl) silyl; or unsubstituted C _1-10 An alkyl group, a carboxyl group,

R ₁₁ to R ₁₆ 、R ₂₁ To R ₂₆ And R ₃₁ To R ₃₅ Each independently is hydrogen; deuterium; unsubstituted tris (C) _1-10 Alkyl) silyl; unsubstituted tris (C) _6-20 Aryl) silyl; unsubstituted or substituted by three (C) _1-10 Alkyl) silyl or tri (C) _6-20 Aryl) silyl substituted di (C) _6-20 Aryl) amino; unsubstituted C _1-10 An alkyl group; or unsubstituted or substituted by three (C) _1-10 Alkyl) silyl or tri (C) _6-20 Aryl) silyl substituted C _6-20 An aryl group, a heteroaryl group,

provided that in one formula R _a1 To R _a5 、R _b1 To R _b5 、R ₁₁ To R ₁₆ 、R ₂₁ To R ₂₆ And R ₃₁ To R ₃₅ At least one of which is unsubstituted tri (C) _1-10 Alkyl) silyl groups, or unsubstituted tri (C) _6-20 Aryl) silyl groups, or by a tri (C) _1-10 Alkyl) silyl or tri (C) _6-20 Aryl) silyl substituted.

3. The compound of claim 2, wherein in formulae 1-2, 1-4, 1-6, and 1-11 to 1-13, in one formula R _a1 To R _a5 、R _b1 To R _b5 、R ₁₁ To R ₁₆ 、R ₂₁ To R ₂₆ And R ₃₁ To R ₃₅ At least one of which is-Si (CH) ₃ ) ₃ or-Si (C) ₆ H ₅ ) ₃ Or by-Si (CH) ₃ ) ₃ or-Si (C) ₆ H ₅ ) ₃ And (4) substitution.

4. The compound of claim 2, wherein in formulas 1-2, 1-4, 1-6, and 1-11 to 1-13, R _a1 To R _a5 And R _b1 To R _b5 Each independently hydrogen, deuterium, -Si (CH) ₃ ) ₃ 、-Si(C ₆ H ₅ ) ₃ 、-CH ₃ 、-CH(CH ₃ ) ₂ or-C (CH) ₃ ) ₃ ，

R ₁₁ To R ₁₆ 、R ₂₁ To R ₂₆ And R ₃₁ To R ₃₅ Each independently hydrogen, deuterium, -Si (CH) ₃ ) ₃ 、-Si(C ₆ H ₅ ) ₃ 、-CH ₃ 、-CH(CH ₃ ) ₂ or-C (CH) ₃ ) ₃ And is selected from:

wherein Ph means phenyl.

5. The compound according to claim 2, wherein the compound represented by formula 1 is represented by any one of the following formulae 1-2A, 1-4A, 1-6A, and 1-11A to 1-13A:

[ formula 1-2A ]

[ formulae 1-4A ]

[ formulae 1-6A ]

[ formulae 1-13A ]

Wherein, in the formulae 1-2A, 1-4A, 1-6A and 1-11A to 1-13A,

X ₁ 、X ₂ 、R _a1 to R _a4 、R _b1 To R _b4 、R ₁₂ 、R ₁₃ 、R ₂₂ 、R ₂₃ And R ₃₂ As defined in claim 2, the first and second,

provided that in one formula R _a1 To R _a4 、R _b1 To R _b4 、R ₁₂ 、R ₁₃ 、R ₂₂ 、R ₂₃ And R ₃₂ At least one of which is-Si (CH) ₃ ) ₃ or-Si (C) ₆ H ₅ ) ₃ Or by-Si (CH) ₃ ) ₃ or-Si (C) ₆ H ₅ ) ₃ And (4) substitution.

6. The compound of claim 1, wherein the compound is any one selected from the group consisting of:

7. an organic light emitting device comprising: a first electrode; a second electrode disposed on an opposite side of the first electrode; and at least one layer of organic material disposed between the first and second electrodes, wherein at least one of the layers of organic material comprises a compound according to any one of claims 1 to 6.

8. An organic light-emitting device according to claim 7, wherein the organic material layer containing the compound is a light-emitting layer, and

the light emitting layer is formed by a vacuum deposition method.

9. An organic light-emitting device according to claim 8, wherein the compound is a dopant material, and

the content of the dopant material is 0.5 to 20 wt% with respect to the total content of the light emitting layer.

10. An organic light-emitting device according to claim 8, wherein the light-emitting layer further comprises a host material, and

the host material is a compound represented by the following formula 3:

[ formula 3]

Wherein, in the formula 3,

ar is C _6-20 Aryl or C containing at least one heteroatom selected from N, O and S _2-60 Heteroaryl, and

n is an integer of 1 to 10.

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